Oxalyl chloride → 2-(6-Methoxynaphthalen-2-yl)propanoyl chloride

HRID 844513Notes

Reaction equation

HRID 844513 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:17])[C:14](O)=[O:15])[CH:7]=[CH:6]2.C(Cl)(=O)C([Cl:21])=O>CN(C=O)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:17])[C:14]([Cl:21])=[O:15])[CH:7]=[CH:6]2

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 156391Naproxen

Product 1

HCID 54916922-(6-Methoxynaphthalen-2-yl)propanoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-6-methoxy-α-methyl-2-naphthaleneacetic acid (23.09 g) and THF (41 mL) is agitated until dissolution is achieved. Oxalyl chloride (17.5 mL) is added to the flask followed by DMF (3 drops) and heptanes (50 mL). The mixture is stirred for approximately 2 hours. The resulting slurry is filtered, washed with heptane (15 mL) and aspirated for 3 minutes and vacuum dried to give 17.44 g.

Workup

  1. stirringThe mixture is stirred for approximately 2 hours
  2. filtrationThe resulting slurry is filtered
  3. washwashed with heptane (15 mL)
  4. customvacuum dried
  5. customto give 17.44 g

Sources & evidence

ORD record
ord-1b9ecbecac02427fbba42a1a7b4a338d
Source dataset
uspto-grants-2002_04
Patent number
US06380388B1

Reaction notes

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